Water → 1-(p-Chlorophenyl)-1-[2-fluoro-3-(m-phenoxyphenyl)propenyl]cyclopropane

Participants

Reaction Conditions

Reaction Steps

p-Toluenesulfonyl chloride (19.07 mg, 0.10 mmol) is added to a solution of 1-(p-chlorophenyl)-α-fluoro-β-hydroxy-α-(m-phenoxybenzyl)cyclopropanepropionic acid having a 9:1 [R,S and S,R] to [R,R and S,S] ratio (20 mg, 0.05 mmol) in pyridine (2 mL). The reaction mixture is heated to 60° C. and poured into water. The aqueous mixture is extracted with diethyl ether. The organic extracts are combined, washed sequentially with 2 N hydrochloric acid, water, 10% sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a colorless oil (18 mg, 100%) which is found to have a 9:1 Z to E ratio by NMR spectral analyses.

Provenance & Evidence